4-Iodotoluene → HCID 18691567, compound

HRID 1600011Notes

Reaction equation

HRID 1600011 reaction equation
C([CH:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)C1C=CC=CC=1.[N+:14]([O-:17])([O-])=[O:15].[K+].I[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1>FC(F)(F)C(O)=O>[N+:14]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:12]2[O:11][C:10](=[O:13])[NH:9][CH2:8]2)=[CH:22][CH:21]=1)([O-:17])=[O:15]

Participants

5

Reactant 3

HCID 122074-IodotolueneHCID 24434Potassium NitrateHCID 5596684-Benzyl-1,3-oxazolidin-2-one

Product 1

HCID 18691567HCID 18691567, compoundYield 495.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-benzyl-2-oxazolidinone (5 g, 28 mmol), potassium nitrate (2.9 g, 29 mmol)and p-iodotoluene (0.5 g, 2 mmol) were stirred in trifluoracetic acid (50 ml) overnight. The mixture was then poured onto ice and extracted with ethyl acetate. This was washed with sodium bicarbonate solution, dried (MgSO4) and evaporated. Flash chromatography (70:30 ethyl acetate/hexane)gave the product (2.2 g, 35%) Mpt 150°-151° C., MS(ES)223 (M+1)+

Workup

  1. additionThe mixture was then poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThis was washed with sodium bicarbonate solution
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d01ed51ed2954a399286df53651edd71
Source dataset
uspto-grants-1998_04
Patent number
US05744466

Reaction notes

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